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Hydrochloric Acid → 6-hydroxy-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester

HRID 1833156
ノート
印刷プレビュー

反応式

HRID 1833156 の反応式
[CH2:1]([O:3][C:4](=[O:25])[N:5]([C:16]1[CH:21]=[CH:20][C:19](O)=[C:18]([O:23][CH3:24])[CH:17]=1)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14]C)[CH:9]=1)[CH3:2].Cl.[C:27](OCC)(=[O:29])C.[CH3:33][CH2:34]CCCC>CC(C)=O.O>[CH2:1]([O:3][C:4]([N:5]1[CH:6]=[CH:7][C:8]2[C:13](=[CH:12][C:11]([O:29][CH3:27])=[C:10]([OH:14])[CH:9]=2)[CH:16]1[CH2:21][C:20]1[CH:34]=[CH:33][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=1)=[O:25])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexaneHCID 867601154-Hydroxy-3-methoxy-phenyl-2-(3-methoxy-phenyl)-ethyl-carbamic acid ethyl ester

生成物 1

HCID 210349376-hydroxy-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester収率 37%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒
HCID 962
Water
溶媒

実験手順

To a stirred solution of (2,2-dimethoxy-ethyl)-[1-(4-hydroxy-3-methoxy-phenyl-2-(3-methoxy-phenyl)-ethyl-carbamic acid ethyl ester (3.7 g, 8.55 mmol) in acetone (150 mL) was added 6N hydrochloric acid (38 mL) at 0° C. The reaction mixture was stirred at room temperature for 15 hrs. The mixture was diluted with water. The solvent was evaporated and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (80 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 50% ethyl acetate/hexane) afforded 6-hydroxy-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester (1.17, 37% yield) as a colorless oil.

後処理

  1. customThe solvent was evaporated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
  3. washThe combined extracts were washed with saturated aqueous sodium chloride solution (80 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7b1cb67951c9470ba915dd69998121ae
出典データセット
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07067529B2

反応ノート

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